For anyone who has worked with Office 365/Azure AD and AADConnect, you will of course be aware that we can now sync passwords two ways from Azure AD to our on-premises AD. This is obviously a very handy thing to do for myriad reasons, and an obvious suggestion for a business intending to utilise Office 365. The conversation with the security bod however, might be a different kettle of fish. In this post, I aim to explain how the password sync and write-back features work, and hopefully arm you with enough information to have that chat with the security guys.

Password Sync to AAD

If you’ve been half-listening to any talks around password sync, the term ‘it’s not the password, it’s a hash of a hash’ is probably the line you walked away with, so let’s break down what that actually means. First up, a quick explanation of what it actually means to hash a value. Hashing a value is applying a cryptographic algorithm to a string to irreversibly convert that string into another sting of a fixed length. This differs from encryption in that with encryption we intend to be able to retrieve the data we have stored, so must hold a decryption key – with hashing, we are unable to derive the original string from the hashed string, and nor do we want to. If it makes no sense to you that we wouldn’t want to reverse a hashed value, it will by the end of this post.

So, in Active Directory when a user sets their password, the value stored is not actually the password itself, it’s an MD4 hash of the password once it’s been converted to Unicode Little Endian format. Using this process, my password “nicedog” ends up in Active Directory as 2993E081C67D79B9D8D3D620A7CD058E. So, this is the first part of the “hash of a hash”.

The second part of the “hash of a hash” is going to go buck wild with the hashing. Once the password has been securely transmitted to AADConnect (I won’t detail that process, because we end up with our original MD4 hash anyway), the MD4 hash is then:

  1. Converted to a 32-byte hexadecimal string
  2. Converted into binary with UTF-16 encoding
  3. Salted with 10 additional bytes
  4. Resultant string hashed and re-hashed 1000 times with HMAC-SHA256 via PBKDF2

So, as you can see, we’re actually hashing the hash enough to make Snoop Dogg blush. Now, we finally have the have the hash which is securely sent to Azure AD via an SSL channel. At this point, the hashed value which we send is so far removed from the original hash that even the most pony-tailed, black tee-shirt and sandal wearing security guy would have to agree it’s probably pretty secure. Most importantly, if Azure AD was ever compromised and an attacker did obtain your users password hashes, they are unable to be used to attack any on-premises infrastructure with a “pass the hash” attack, which would be possible if AD’s ntds.dit was compromised and password hashes extracted.

So now Azure AD has these hashes, but doesn’t know your passwords – how are user’s passwords validated? Well it’s just a matter of doing the whole thing again with a user provided password when that user logs on. The password is converted, salted, hashed and rehashed 1000 times in the exact same manner, meaning the final hash is exactly the same as the one stored in Azure AD – the two hashes are compared, and if we have a match, we’re in. Easy. Now let’s go the other way.

Password Write-back to AD

So how does it work going back the other way? Differently. Going back the other way, we can’t write a hash ourselves to Active Directory, so we need to get the actual password back from AAD to AD and essentially perform a password reset on-prem allowing AD to then hash and store the password. There are a couple of things which happen when we install AADConnect and enable Password Write-back to allow us to do this

  1. Symmetric keys are created by AAD and shared with AADConnect
  2. A tenant specific Service Bus is created, and a password for it shared with AADConnect

The scenario in which we are writing a password back from AAD to AD is obviously a password reset event. This is the only applicable scenario where we would need to, because a password is only set in AAD if that user is “cloud only”, so they would of course not have a directory to write back to. Only synced users need password write-back, and only upon password reset. So AAD gets the password back on-premises by doing the following:

  1. User’s submitted password is encrypted with the 2048-bit RSA Key generated when you setup write-back
  2. Some metadata is added to the package, and it is re-encrypted with AES-GCM
  3. Message sent to the Service Bus via and SSL/TLS channel
  4. On-premises AADConnect agent wakes up and authenticates to Service Bus
  5. On-premises agent decrypts package
  6. AADConnect traces cloudanchor attribute back to the connected AD account via the AADConnect sync engine
  7. Password reset is performed for that user against a Primary Domain Controller

So, that’s pretty much it. That’s how we’re able to securely write passwords back and forth between our on-premises environment and AAD without Microsoft ever needing to store a user’s password. It’s worth noting for that extra paranoid security guy though that if he’s worried about any of the encryption keys or shared passwords being compromised, you can re-generate the lot simply by disabling and re-enabling password writeback.

Hopefully this post has gone some way towards helping you have this particular security conversation, no matter what year the security guys Metallica tour tee-shirt is from.

Azure Infrastructure, Identity and Access Management, Office 365, Security

Join the conversation! 4 Comments

  1. Informative AND witty

  2. So I would hazzard a guess that due to the way it write back, anyone uses GAPS, (Google Apps Password Sync) will not change the password in Google?

  3. The ultimate outcome would be if PCNS could also capture the AAD Connect written back password & send it to other targets, for instance other AD Forests where the identity also resides. Unfortunately as far as I understand this is not possible


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